Gold (I/III)-Catalyzed Trifluoromethylthiolation and Trifluoromethylselenolation of Organohalides

Sagar R Mudshinge; Yuhao Yang; Bo Xu; Gerald B Hammond; Zhichao Lu

doi:10.1002/anie.202115687

Gold (I/III)-Catalyzed Trifluoromethylthiolation and Trifluoromethylselenolation of Organohalides

Angew Chem Int Ed Engl. 2022 Mar 14;61(12):e202115687. doi: 10.1002/anie.202115687. Epub 2022 Feb 3.

Authors

Sagar R Mudshinge¹, Yuhao Yang¹, Bo Xu², Gerald B Hammond¹, Zhichao Lu¹

Affiliations

¹ Department of Chemistry, University of Louisville, Louisville, KY 40292, USA.
² College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 2999 North Renmin Lu, Shanghai, 201620, China.

Abstract

The first C-SCF₃ /SeCF₃ cross-coupling reactions using gold redox catalysis [(MeDalphos)AuCl], AgSCF₃ or Me₄ NSeCF₃ , and organohalides as substrates are reported. The new methodology enables a one-stop shop synthesis of aryl/alkenyl/alkynyl trifluoromethylthio- and selenoethers with a broad substrate scope (>60 examples with up to 97 % isolated yield). The method is scalable, and its robustness is evidenced by the late-stage functionalization of various bioactive molecules, which makes this reaction an attractive alternative in the synthesis of trifluoromethylthio- and selenoethers for pharmaceutical and agrochemical research and development.

Keywords: Cross-Coupling; Gold Catalysis; Organohalides; Trifluoromethylselenolation; Trifluoromethylthiolation.

Publication types

Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Catalysis
Gold*
Oxidation-Reduction

Substances

Gold

Abstract

Publication types

MeSH terms

Substances

Grants and funding